Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | 4-Nitro-1,3-benzenediamine | HCID 21208 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66966094 | HCID 66966094 | — |
Reaction Steps
To a solution of 4-nitro-benzene-1,3-diamine (1.6 g) in acetonitrile (20 mL) was added NaHCO3 (1 g) and ethyl chloroformate (1.0 mL). The mixture was heated at 75° C. with stirring overnight. Cooled to ambient temperature, the mixture was diluted by water and extracted twice with ethyl acetate. Combined organics were dried over Na2SO4, filtered, and concentrated to give crude yellow solid. Trituration from dichloromethane afforded (3-amino-4-nitro-phenyl)-carbamic acid ethyl ester: 1H NMR (400 MHz, CD3OD) 7.9 (d, 1H), 7.3 (s, 1H), 6.5 (d, 1H), 4.2 (q, 2H), 1.3 (t, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08222248B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-e9a06b9ee9aa4e48858463d4e7987f0f |
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| Source note | uspto-grants-2012_07 |
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